Tetrahydrofuran → (2-[4-(1-Ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenoxy]-1H-benzimidazol-1-yl]ethanol

HRID 573319노트

반응식

HRID 573319 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:9]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]2[CH:39]=[CH:38][C:21]([O:22][C:23]3[N:27](CC(OCC)=O)[C:26]4[CH:34]=[CH:35][CH:36]=[CH:37][C:25]=4[N:24]=3)=[CH:20][CH:19]=2)=[N:10]1)[CH3:8].[O-]S([O-])(=O)=O.[Na+].[Na+].C1C[O:50][CH2:49][CH2:48]1>>[CH2:7]([N:9]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]2[CH:19]=[CH:20][C:21]([O:22][C:23]3[N:27]([CH:49]([OH:50])[CH3:48])[C:26]4[CH:34]=[CH:35][CH:36]=[CH:37][C:25]=4[N:24]=3)=[CH:38][CH:39]=2)=[N:10]1)[CH3:8]

참가 물질

5

반응물 4

HCID 8028TetrahydrofuranHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 66727897Ethyl {2-[4-(1-ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenoxy]-1H-benzimidazol-1-yl}acetate

생성물 1

HCID 86688980(2-[4-(1-Ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenoxy]-1H-benzimidazol-1-yl]ethanol

실험 절차

LiAlH4 (24.8 mg) was added to a solution of ethyl 2-{2-[4-(1-ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenoxy]-1H-benzo[d]imidazol-1-yl}acetate (144 mg) in THF (3.5 ml) at 0° C. After stirring for 1 h at the same temperature, Na2SO4.10H2O was added to the reaction mixture at 0° C. and stirred for 30 min. After Na2SO4 was added to this mixture, the precipitate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane). The solid was crystallized from AcOEt/hexane to give the title compound (81 mg).

후처리

  1. additionwas added to the reaction mixture at 0° C.
  2. customthe precipitate was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)
  5. customThe solid was crystallized from AcOEt/hexane

출처 및 근거

ORD 기록
ord-b27b4afb252f4bd6bb313a3265dbe281
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029536B2

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